New 4-chloromethyl-6-hydroxycoumarins have been obtained by the condensation of hydroquinone derivatives with 4-chloroacetoacetic ester, and have been used for the synthesis of 4-(2-benzofuryl)-6-hydroxycoumarins. Alkylation and acylation of the phenolic hydroxyl of the synthesized 4-(2-benzo-furyl)coumarins have been investigated.
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References
G. V. M. Sharma, J. J. Reddy, P. S. Lakshmi, and P. R. Krishna, Tetrahedron Lett., 46, 6119 (2005).
S. D. Joshi and R. N. Usgaonkar, Indian J. Chem. 21B, 399 (1982).
F. Leonetti, A. Favia, A. Rao, R. Aliano, A. Paluszcak, R. W. Hartmann, and A. Carotti, J. Med. Chem., 47, 6792 (2004).
R. Dey, J. Indian Chem. Soc., 11, 635 (1934).
P. Waykole and R. N. Usgaonkar, Indian J. Chem. 21B, 707 (1982).
Y. Fall, L. Santana, M. Teijeira, and E. Uriarte, Heterocycles, 41, 647 (1995).
A. P. Silva, H. Q. N. Gunaratne, P. L. M. Lynch, A. J. Patty, and G. L. Spence, J. Chem. Soc., Perkin Trans. 2, 1611 (1993).
G. Renzi, A. Scozzafava, and C. T. Supuran, Bioorg. Med. Chem. Lett., 10, 673 (2000).
A. Long, J. Parrick, and R. J. Hodgkiss, Synthesis, 709 (1991).
S. P. Bondarenko, M. S. Frasinyuk, and V. P. Khilya, Khim. Prir. Soedin., 206 (2003).
M. S. Frasinyuk, S. P. Bondarenko, and V. P. Khilya, Khim. Prir. Soedin., 117 (2006).
S. Hanmantgad, M. Kulkarnti, V. Patil, P. Diwan, and D. Kulkarnti, Indian J. Chem., 25B, 779 (1986).
A. R. Deshpande, U. K. Joshi, and M. V. Paradkar, Indian J. Chem., 27B, 524 (1988).
K. Y. Anklekar, C. D. Lakkannavar, G. M. Kulkarni, and M. V. Kulkarni, Indian J. Chem., 42B, 1548 (2003).
M. Ghate, D. Manohar, V. Kulkarni, R. Shobha, and S. Y. Kattimani, Eur. J. Med. Chem., Chim. Ther., 38, 297 (2003).
I. A. Khan and M. V. Kulkarni, Indian J. Chem., 38B, 491 (1999).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 361–369, March, 2009.
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Frasinyuk, M.S., Bondarenko, S.P. & Khilya, V.P. Synthesis and properties of 4-chloromethyl-6-hydroxy-coumarins and 4-(2-benzofuryl)-6-hydroxycoumarins. Chem Heterocycl Comp 45, 290–296 (2009). https://doi.org/10.1007/s10593-009-0275-x
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DOI: https://doi.org/10.1007/s10593-009-0275-x